反应详情

温度

60 °C

tert-Butyl nitrite (90%, 2 mL, 14.8 mmol) was added to a stirred solution of amine 19 (1.0 g, 4.95 mmol) in DMF (50 mL) at 60° C. and the solution stirred at 60° C. for 2 h. The solution was cooled to 20° C. and the solvent evaporated. The residue was partitioned between EtOAc (150 mL) and water (150 mL), the organic fraction was washed with water (2×50 mL), washed with brine (50 mL) and dried and the solvent evaporated. The residue was purified by chromatography, eluting with 10% EtOAc/DCM, to give 1-oxide 64 (401 mg, 43%) as a white solid: mp (EtOAc/pet. ether) 130-131° C.; 1H NMR δ 8.91 (s, 1H, H-3), 8.28 (s, 1H, H-9), 7.82 (s, 1H, H-5), 3.11-3.19 (m, 4H, H-6, H-8), 2.24 (p, J=7.5 Hz, 2H, H-7); 13C NMR δ 154.9, 153.0, 150.0, 147.3, 134.6, 123.2, 114.4, 33.2, 32.9, 25.7. Anal. calcd for C10H9N3O: C, 64.2; H, 4.9; N, 22.5. Found: C, 64.1; H, 4.9; N, 22.5%.

1. temperatureThe solution was cooled to 20° C.
2. customthe solvent evaporated
3. customThe residue was partitioned between EtOAc (150 mL) and water (150 mL)
4. washthe organic fraction was washed with water (2×50 mL)
5. washwashed with brine (50 mL)
6. customdried
7. customthe solvent evaporated
8. customThe residue was purified by chromatography
9. washeluting with 10% EtOAc/DCM